Acenaphthylene-1,2-dione

In a catalyst-free, aqueous-mediated MCR facilitated by sonication, isat-ins 200, 5-amino-3-methylpyrazole 201 and a-mercaptoacetic acids 202 reacted to form spiro(indole-3,4 -pyrazolo[3,4-e][l,4]thiazepines) 203 in high yield. Replacement of the isatin with acenaphthylene-1,2-dione or N-substitued piperidin-4-ones gave the corresponding spiro(pyrazolo-1,4-thiazepines) (13RA18992). 

In related work, the same researchers described a four-component domino reaction that allows the one-pot synthesis of highly complex spiro systems, i.e. spiro[indoline/acenaphthylene-3,4-pyrazolo[3,4-6]pyridine derivatives 59 and 60 from phertylhydrazine, 3-aminocrotononitrile, isatin or acenaphthylene-1,2-dione and cyclic 1,3-dicarbonyl compoimds, including cyclohexane-l,3-diones and barbituric or thiobaibituric acid, in the presence of ( )-camphor-10-sulphonic acid (CSA) as catalyst (Scheme 1.30). 

Whereas plausible fungal metabolites from anthracene, acenaphthylene, fluorene, and benz[fl]anthracene—anthracene-9,10-quinone, acenaphthene-9,10-dione, fluorene-9-one, and benz[fl]anthracene-7,12-quinone—were found transiently in compost-amended soil, these were formed even in sterile controls by abiotic reactions (Wischmann and Steinhart 1997). 

Photochemical cycloaddition of cyclohex-2-ene-l,4-dione (31) and acenaphthylene (32) in dichloromethane gives the iM-,un//,c -adduct 33 in 15% yield, in addition to large amounts of acenaphthylene dimers, which are insoluble and precipitate during the photolysis.100... 

Also, Rezaei et al. reported a facile and efficient one-pot three-component ultrasound-promoted synthesis of spiroacenaphthylene pyrazolotriazoles (184) and pyr-azolophthalazines (185) via a three-component reaction of various nitrile-contained acidic C-H (182), acenaphthylene-l,2-dione (159), and phthalhydrazide (49) or 4-phenyl-l,2,4-triazolidine-3,5-dione (183) in the presence of EtjN as the catalyst (Scheme 8.60). 

L. Wang, W. Wang, 1. Cuui, W. Ren, N. Meng, 1. Wang, X. Qian, Preparation of chiral trans-5-substituted-acenaphthene-l,2-diols by Baker s yeast-mediated reduction of 5-substituted-acenaphthylene-l,2-diones. Tetrahedron Asymm. 21 (2010) 825-830. 

---